1-(2,4-Dichloro-benzyl-idene)-4-ethyl-thio-semicarbazide.

The title compound, C(10)H(11)Cl(2)N(3)S, was prepared by the reaction of 4-ethyl-thio-semicarbazide and 2,4-dichloro-benzaldehyde. It is approximately planar, the dihedral angle between the benzene ring and the thio-urea unit being 8.43 (18)°. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For background to Schiff bases, see: Casas et al. (2000 ▶). For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C10H11Cl2N3S

M = 276.18

Monoclinic,

a = 5.4339 (11) Å

b = 20.526 (4) Å

c = 11.313 (2) Å

β = 101.97 (3)°

V = 1234.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

10913 measured reflections

2707 independent reflections

1416 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.187

S = 0.92

2707 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035671/hb5632sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035671/hb5632Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H11Cl2N3S	F(000) = 568
Mr = 276.18	Dx = 1.486 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1416 reflections
a = 5.4339 (11) Å	θ = 3.5–27.5°
b = 20.526 (4) Å	µ = 0.67 mm−1
c = 11.313 (2) Å	T = 293 K
β = 101.97 (3)°	Block, colorless
V = 1234.4 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1416 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.109
graphite	θmax = 27.5°, θmin = 3.5°
phi and ω scans	h = −6→6
10913 measured reflections	k = −26→26
2707 independent reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2707 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	−0.1063 (2)	0.99987 (6)	0.79802 (13)	0.0434 (4)
Cl2	0.7303 (2)	0.85591 (6)	1.34950 (13)	0.0499 (4)
Cl1	1.4115 (2)	0.70212 (6)	1.20880 (15)	0.0558 (4)
N3	0.4756 (6)	0.90330 (15)	0.9707 (4)	0.0355 (9)
N2	0.2667 (7)	0.94274 (17)	0.9454 (4)	0.0390 (9)
H2A	0.2030	0.9583	1.0029	0.047*
N1	0.2795 (7)	0.93533 (18)	0.7450 (4)	0.0410 (10)
H1A	0.4117	0.9118	0.7681	0.049*
C5	0.7795 (7)	0.84768 (18)	1.1156 (4)	0.0317 (10)
C3	0.1623 (7)	0.95672 (19)	0.8288 (4)	0.0324 (10)
C8	1.1713 (8)	0.7596 (2)	1.1742 (5)	0.0381 (11)
C9	1.0643 (8)	0.78286 (19)	1.2644 (5)	0.0393 (12)
H9A	1.1209	0.7695	1.3440	0.047*
C4	0.5640 (8)	0.89200 (19)	1.0829 (5)	0.0373 (11)
H4A	0.4932	0.9114	1.1423	0.045*
C7	1.0936 (9)	0.7793 (2)	1.0562 (5)	0.0418 (12)
H7A	1.1715	0.7632	0.9964	0.050*
C10	0.8684 (8)	0.82717 (19)	1.2342 (4)	0.0332 (10)
C6	0.8994 (8)	0.8232 (2)	1.0276 (5)	0.0384 (11)
H6A	0.8471	0.8368	0.9480	0.046*
C2	0.2011 (10)	0.9487 (3)	0.6169 (5)	0.0492 (13)
H2B	0.2201	0.9949	0.6029	0.059*
H2C	0.0246	0.9377	0.5906	0.059*
C1	0.3510 (11)	0.9109 (3)	0.5440 (6)	0.0641 (16)
H1B	0.2935	0.9209	0.4599	0.096*
H1C	0.3306	0.8651	0.5567	0.096*
H1D	0.5255	0.9223	0.5686	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0362 (7)	0.0577 (7)	0.0350 (8)	0.0114 (4)	0.0044 (5)	0.0005 (5)
Cl2	0.0628 (8)	0.0614 (7)	0.0280 (8)	0.0123 (5)	0.0151 (6)	0.0009 (6)
Cl1	0.0561 (8)	0.0551 (7)	0.0546 (11)	0.0202 (5)	0.0078 (7)	0.0014 (6)
N3	0.037 (2)	0.0394 (19)	0.030 (3)	0.0028 (13)	0.0062 (17)	0.0035 (16)
N2	0.039 (2)	0.051 (2)	0.026 (3)	0.0122 (15)	0.0047 (17)	0.0013 (17)
N1	0.037 (2)	0.054 (2)	0.030 (3)	0.0091 (15)	0.0019 (18)	0.0029 (18)
C5	0.039 (2)	0.030 (2)	0.025 (3)	−0.0023 (15)	0.0038 (19)	0.0018 (17)
C3	0.031 (2)	0.040 (2)	0.026 (3)	−0.0020 (16)	0.0043 (19)	−0.0015 (18)
C8	0.040 (2)	0.038 (2)	0.034 (3)	0.0015 (17)	0.003 (2)	−0.0022 (19)
C9	0.045 (3)	0.041 (2)	0.029 (3)	0.0050 (17)	−0.001 (2)	0.0030 (19)
C4	0.038 (2)	0.042 (2)	0.030 (3)	0.0049 (17)	0.004 (2)	−0.0011 (19)
C7	0.045 (3)	0.047 (2)	0.035 (3)	0.0042 (18)	0.012 (2)	−0.007 (2)
C10	0.041 (2)	0.037 (2)	0.022 (3)	0.0003 (16)	0.0089 (19)	−0.0005 (18)
C6	0.045 (3)	0.047 (2)	0.023 (3)	0.0012 (18)	0.005 (2)	−0.003 (2)
C2	0.055 (3)	0.066 (3)	0.025 (3)	0.011 (2)	0.004 (2)	0.004 (2)
C1	0.057 (3)	0.099 (4)	0.038 (4)	0.015 (3)	0.013 (3)	−0.004 (3)

S1—C3	1.681 (4)	C8—C7	1.376 (7)
Cl2—C10	1.738 (5)	C9—C10	1.388 (6)
Cl1—C8	1.743 (4)	C9—H9A	0.9300
N3—C4	1.282 (6)	C4—H4A	0.9300
N3—N2	1.375 (5)	C7—C6	1.373 (6)
N2—C3	1.354 (6)	C7—H7A	0.9300
N2—H2A	0.8600	C6—H6A	0.9300
N1—C3	1.322 (6)	C2—C1	1.491 (7)
N1—C2	1.449 (7)	C2—H2B	0.9700
N1—H1A	0.8600	C2—H2C	0.9700
C5—C6	1.392 (7)	C1—H1B	0.9600
C5—C10	1.393 (6)	C1—H1C	0.9600
C5—C4	1.468 (6)	C1—H1D	0.9600
C8—C9	1.362 (7)
C4—N3—N2	115.8 (4)	C6—C7—C8	119.2 (5)
C3—N2—N3	119.2 (4)	C6—C7—H7A	120.4
C3—N2—H2A	120.4	C8—C7—H7A	120.4
N3—N2—H2A	120.4	C9—C10—C5	122.1 (4)
C3—N1—C2	124.7 (4)	C9—C10—Cl2	117.8 (4)
C3—N1—H1A	117.7	C5—C10—Cl2	120.2 (3)
C2—N1—H1A	117.7	C7—C6—C5	121.3 (5)
C6—C5—C10	117.3 (4)	C7—C6—H6A	119.3
C6—C5—C4	120.7 (4)	C5—C6—H6A	119.3
C10—C5—C4	121.9 (4)	N1—C2—C1	111.9 (4)
N1—C3—N2	117.5 (4)	N1—C2—H2B	109.2
N1—C3—S1	123.6 (4)	C1—C2—H2B	109.2
N2—C3—S1	118.9 (4)	N1—C2—H2C	109.2
C9—C8—C7	122.1 (4)	C1—C2—H2C	109.2
C9—C8—Cl1	119.0 (4)	H2B—C2—H2C	107.9
C7—C8—Cl1	118.8 (4)	C2—C1—H1B	109.5
C8—C9—C10	118.0 (5)	C2—C1—H1C	109.5
C8—C9—H9A	121.0	H1B—C1—H1C	109.5
C10—C9—H9A	121.0	C2—C1—H1D	109.5
N3—C4—C5	118.5 (5)	H1B—C1—H1D	109.5
N3—C4—H4A	120.8	H1C—C1—H1D	109.5
C5—C4—H4A	120.8

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.86	2.56	3.409 (5)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.56	3.409 (5)	168

Symmetry code: (i) .